The Four-Carbon Saccharinic Acids

Abstract

This chapter discusses the four-carbon saccharinic acids. When an aqueous solution of a carbohydrate is treated with a base, carbohydrate substances known as “saccharinic acids” are produced. During the oxidation of maltose in alkaline solution, an acid had been produced whose phenylhydrazide had an analysis agreeing perfectly with that calculated for a four-carbon saccharinic acid. The properties of the free acid were those that would be expected of one of these acids. Its configuration could not, however, be reported at that time because of the absence of data as to the properties and constants of the four-carbon saccharinic acids. The chapter describes the synthesis of the four-carbon saccharinic acids that includes: (1) 3,4-dihydroxybutanoic acids, (2) 2 ,4-dihydroxybutanoic acids, (3) 2 ,3-dihydroxybutanoic acids, and (4) 3-hydroxy-2-(hydroxymethyl)propanoic acid. 2,4-Dihydroxybutanoic acid, a 3-deoxytetronic acid, is the only theoretically possible four-carbon metasaccharinic acid ; it was isolated by Nef in the DL form in the course of his work on the action of sodium hydroxide on D-arabinose. It therefore constitutes the only four-carbon saccharinic acid isolated to date from a sugar-alkali reaction.